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$3,750,000
4 Beds 4 Baths ML82051481 MLS
Don't Miss the latest updates. Located in a community renowned for exceptional schools, this is a compelling Hillsborough opportunity. Offered at the lowest price per sq. ft. in Hillsborough, it delivers outstanding value in the community & across the Peninsula. Sweeping Bay & San Mateo Bridge views define this home. It features newly painted interiors, hardwood floors & a dramatic great room w/walls of glass overlooking the pool, expansive deck & panoramic viewsan exceptional setting for everyday living & entertaining. Designed for multigenerational living , w/ADU potential, the home offers 2 kitchens, 2 laundry rooms, separate exterior access & living & work-from-home spaces. Main level includes 2 primary suites, powder rm & view kitchen w/stone countertops, generous island, eating area & fireplace. Nearby office offers potential for a 5th BR or primary suite expansion. Lower level includes 2 BRs, full BA, 2nd kit/dining area & flexible bonus room ideal as a 2nd office or craft room. Direct patio, pool & outdoor access makes this level ideal for extended family, guests, caregivers or independent living. Wine cellar, workshop, 2-car garage, oversized driveway & generous storage complete this rare offering w/exceptional views, impressive scale, versatility & unmatched value.

1407 Carlton RD, Hillsborough

Listed by Samia Morgan, 650-678-3633 from eXp Realty of Northern California, Inc.
(If provided) CoList: from

$5,200,000
4 Beds 4 Baths ML82046360 MLS
This stunning Chateau-style residence is gracefully situated on coveted Chateau Drive in the prestigious Carolands area of Hillsborough. Set on approximately .77 acres of gated grounds with Bay views, a circular driveway, and lush mature landscaping, this private estate is offered for the first time since its original construction. Spanning over 4,200 square feet, the home reflects timeless architecture, grand proportions, and light-filled interiors. A gracious entry opens to an expansive living room anchored by a marble fireplace, an adjoining library, and dramatic arched windows framing serene views. The elegant dining room with coffered ceilings and intricate hardwood floors is ideal for entertaining, while multiple covered verandas create seamless indoor-outdoor living. The home offers 4 bedrooms and 3.5 bathrooms, including a lower-level retreat with closet, fireplace, and patio access, well suited for guests, a private office, or extended living. Featuring a spacious family room, dry sauna, 3 fireplaces, dual laundry areas, and a 3-car garage w/ additional driveway parking. Mostly level grounds enhanced with fruit trees offer potential for a pool or ADU, creating a private estate-like setting. A rare offering in a premier sought after location.

555 Chateau DR, Hillsborough

Listed by Tim Allen Alevizos, 650-255-7635 from Remax Capital
(If provided) CoList: from

Sold listing courtesy of Shuo Xiang from XLB

$10,750,000
7 Beds 6 Baths ML82044447 MLS
Modern Sanctuary in Lower South Hillsborough. Welcome to 655 Hayne Road, a newly completed modern residence offering privacy and refined California living in one of Hillsboroughs most desirable neighborhoods. Set behind a gated entrance on a mostly flat, usable parcel, the property is thoughtfully designed for seamless indoor-outdoor living. The main residence flows primarily across a single level, with an open-concept layout that connects effortlessly to the grounds and frames serene treetop views. Positioned just off the main living areas, the attached ADU offers a natural extension of the home, well suited for entertaining, guests, or extended stays. With easy access to the pool and outdoor kitchen, it lives as a cabana-style retreat, enhancing the indoor-outdoor lifestyle. A separate lower-level space offers flexibility for a home theater, gym, or game room. The grounds are carefully composed to create a true sense of escape, blending manicured landscaping, open turf areas, and a natural backdrop. Ideally located just moments from South School and with convenient access to Burlingame, San Mateo, and major commute routes. A rare offering that pairs modern design with usable land in a sought-after Hillsborough setting, ideal for refined indoor-outdoor living.

655 Hayne RD, Hillsborough

Listed by Shaun Walter, 650-727-4888 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Shaun Walter from CBR

$7,100,000
5 Beds 4 Baths ML82033175 MLS
EPIC HOMAGE TO CRAFTSMANSHIP AND LIFE IN THE SUN...One of Hillsborough's Most Elite Custom Remodels, steeped in the Magic of Montecito and Palm Beach. Every inch meticulously curated of high-end caliber inside and out. Ultimate privacy heightens soaring views above canyon, ridgelines, and sun-blessed luminosity. Top flight luxury designer elements of Venetian plaster walls, vaulted ceilings of 14-15 feet, European tilework, mahogany doors, and made-to-order light fixtures by Steven Handelman of Santa Barbara. Wolf, Sub-Zero, Miele, exquisite custom cabinetry, & more. Indoor/Outdoor celebration as a personal resort with saltwater PebbleSheen pool, 3 waterfalls & raised spa. Flat grassy yards, barbecue cove, secret Napa garden of fruit orchard & irrigated veggie beds. The beauty of the floorplan includes 4 bedrooms on the main level, plus private lower level for 5th bedroom, huge media room & 2nd kitchen. This level is the perfect in-law apartment, teen hangout, or poolside media lounge. And shhhh, don't forget the world-class temp-controlled wine cellar as your own speakeasy! Prestige cul-de-sac location within minutes of Nueva & West Schools, & easy Hwy 280 connection to VC realm of Silicon Valley, plus AI, private equity, & biotech of South San Francisco and Financial District.

25 Searsville CT, Hillsborough

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Chris Iverson from DP

$5,300,000
3 Beds 4 Baths ML82026991 MLS
A Modern Transformation with Sweeping Bay Views! Beautifully remodeled for modern living, this Lower Hillsborough home showcases an open-concept design with wide expanses of glass that frame views across the San Francisco Bay and out to the Bay Bridge and East Bay hills. Natural light fills every room, two gas fireplaces add warmth, and wood-like tile floors unify the open living areas. Expansive formal rooms are complemented by a designer kitchen and family room combination, creating an ideal layout for entertaining and everyday comfort. Rounding out the main level are three spacious bedrooms, including a primary suite that takes full advantage of the views, plus there is a flexible-use lower level with large bonus room and adjoining bath. Outside, an expansive view deck with cable-strung railings and terraced lawns extend the living space, providing ample room for entertaining and play. With its modern transformation, dazzling views, and sought-after Lower Hillsborough setting, this home presents the perfect place to live midway between San Francisco and Silicon Valley.

442 El Arroyo RD, Hillsborough

Listed by Mark Johnson, 650-685-7648 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Max Lo from GRBA

$6,780,000
7 Beds 6 Baths ML82023191 MLS
Vista Southdown: Private Sanctuary, Panoramic Views Main Residence: 6 Bedrooms & 4 Bathrooms | Luxury Dual Story Casita ADU: 1 Bedroom & 2 Bathroom | 5,065 +/- SQ FT | Chefs Kitchen: Thermador Appliances with Dual Wine Fridges & Stone Countertops | Outdoor Paradise: Resort-Style Pool & Spa, BBQ & Sport Court | Bay Views & Lush Grounds: Breathtaking Bay Panoramas, Curated Landscaping and Refined Outdoor Lighting | Primary Ensuite with Large Soaking Tub and Stall Shower | Modern Flooring | Centralized Heating and A/C | Discreetly Protected: Advanced Surveillance Ensuring Comfort and Privacy Nestled among the redwoods with sweeping views of San Francisco and the San Mateo Bridge, 1221 Southdown Road is a modern Hillsborough estate that balances timeless design with contemporary living. Reimagined by designer Ashley Canty, this residence is a statement of style, comfort, and California luxury. The grounds mirror the elegance of the interiors, featuring a sparkling pool and spa, covered loggia, landscaped play areas, turf field, and private terraces for relaxation or recreation. Natural palettes & refined finishes root the home in its hillside setting, with stone, wood, and glass framing the beauty of the landscape. California living at its finest.

1221 Southdown, Hillsborough

Listed by Cullinan Luxury, 650-773-2321 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

$12,600,000
5 Beds 5 Baths ML82021202 MLS
HILLSBOROUGH'S MOST EXCITING NEW CONSTRUCTION! Brand New Designer Showcase Overlooking the Bay near Nueva School. Dream Team of design and craftsmanship: award-winning San Francisco designer Studio Michael Hilal infuses cutting-edge modern DNA with warmth, livability, and a symphony of handpicked accoutrements. Custom builder Nejasmich Developments delivers renowned detail and artistry to a sleek canvas by Sausalito architect Brooks McDonald. The INNOVATION begins with a one-story building envelope. This platform sets the stage for ceilings over 12 feet, and 360 DEGREES OF LUXURY, with dynamic flow to usable flat lands at both front & rear. SEAMLESS is a most fitting theme for this lifestyle. Minimize the boundaries of indoors & outdoors, seamless attention to clean lines & finishes harmonizes as organic ambiance. | European Luxe meets Eastern Minimalism| Showstopper Great Room | Bay-View Party Terrace off Dining Room | 4 beds, 3.5 baths, plus Office, + Family Den in main home | Deluxe ADU for sleeping quarters, kitchen/laundry | Pro quality Gym w/ morning bar, German Sauna, backlit mirrors | Decadent Wine Pantry | Premium millwork of white oak & walnut, curated designer lighting | 3 Steam Showers | Pewter-Flamed Limestone hardscape | Gated Entry | Fire Pit | Outdoor Grilling Hub

55 Del Monte DR, Hillsborough

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: Mike Bohnert from Coldwell Banker Realty

Sold listing courtesy of Kristopher Mares from KWPEN

$8,000,000
5 Beds 5 Baths ML82020606 MLS
Experience the perfect blend of luxury, elegance & California living in this breathtaking Mediterranean estate. This residence offers unparalleled privacy & sweeping views of the San Francisco Bay & surrounding mountains. A long, gated driveway welcomes you setting the stage for the home's elegant interior. Step inside to a dramatic, light-filled foyer featuring a graceful winding staircase that leads into an expansive living room framed by floor-to-ceiling windows showcasing the spectacular views.The gourmet chef's kitchen is comes complete with a large center island, elegant stone countertops, & top-of-the-line Viking stainless steel appliances. A richly wood-paneled library/office & spacious formal living & dining areas add sophistication, while new double-pane windows enhance comfort & energy efficiency throughout the home.Upstairs a primary suite awaits, featuring a spa-inspired bath with a jetted soaking tub, alongside generously sized bedrooms offering comfort & privacy. The impeccably landscaped grounds create a true oasis, featuring a resort-style pool & spa, & private tennis court. Perfect for both relaxation & entertaining, this property offers an unmatched lifestyle in one of California's most coveted settings.

75 Eugenia WAY, Hillsborough

Listed by Donald Kung, 650-219-8700 from Remax Capital
(If provided) CoList: from

Sold listing courtesy of Cici Wang from CBR

$9,350,000
5 Beds 6 Baths ML82012753 MLS
Welcome to Villa De Pinehill an exceptional Mediterranean masterpiece nestled on nearly two acres of enchanting, Italian-inspired gardens. Spanning three stories, this estate is a harmonious blend of timeless elegance and modern sophistication. Inside, exquisite craftsmanship is on full display with custom woodwork, premium natural stone, and globally sourced materials that infuse each space with old-world charm and refined luxury. A grand entrance sets the tone for the expansive interiors, featuring soaring ceilings, generously scaled rooms, and a chefs kitchen with a large island that flows seamlessly to the outdoor lawn and detached guest house. The lower level is designed for entertaining, complete with a wine room, full bar, and flexible bonus space. Multiple balconies and terraces overlook the gated, resort-like grounds. Additional amenities include radiant heating, a security system, an outdoor kitchen, three fireplaces, and a hot tub. A private one-bedroom guest house, with its own eat-in kitchen offers an ideal retreat for guests all set within a coveted enclave of equally stunning estates. Main house 7710sqft + guest house 640 sqft

414 Pinehill RD, Hillsborough

Listed by Phil Chen, 415-271-1920 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Phil Chen from SGP

$3,970,000
4 Beds 3 Baths ML82008148 MLS
CONTEMPORARY CLASSIC WITH A SCENIC GARDEN JOURNEY: Tucked away on a prestigious and rarely offered street, 1431 Carlton Road takes you on a trip where each stop reveals the beauty of the entire journey. The story begins at the heart of Hillsborough, the scenic Lower Lakeview area where canyon crests join jetliner Bay views, and the ambiance feels perfectly lost in time. Circa 1948 Hillsborough, when this home was crafted on a vista plateau, was an exciting period where contemporary designs began blending with traditional, and the inflections of Mid Century started to stylishly inform family comfort. *4 huge bedrooms, plus Office or possible 5th bedroom *Awesome indoor/outdoor flow with rooms stepping out to flat patio, flat lawn, and some Bay view *Recently refreshed with new landscaping, beautiful hardwood floors, designer paint palette and more *Stately living room with 9ft. ceilings, 25 feet long, Bay-view picture windows and yard access *Fabulous new hardscape and lawns *Double Primary Suites on main level (plus Office) plus 2 enormous beds upstairs with 14 ft. vaulted ceilings *Secret side orchard for possible future pool, ADU, or deluxe Bocci Court! *Quiet street of Lower Lakeview 0.9 mile to West School, 1.0 mile to 280 on-ramp, 2.1 mile to Nueva Hillsborough campus.

1431 Carlton RD, Hillsborough

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Robin Li from BQG

$3,700,000
4 Beds 3 Baths ML82007005 MLS
Tucked away at the end of a quiet cul-de-sac in Hillsborough's prestigious Tobin Clark Estate, 35 Anguido Court offers refined living, expansive views, and a thoughtfully designed layout. A paver driveway leads to a stately portico and spacious foyer. The bright formal living room features a wall of windows, elegant fireplace, recessed lighting, and hardwood floors throughout. A formal dining room with large picture windows complements the well-appointed kitchen with granite countertops, stainless steel appliances, and ample cabinetry. The adjacent breakfast nook captures sweeping views from the Hillsborough hills to the SF Bay and opens to two balconies--ideal for outdoor dining. The primary suite includes balcony access, a walk-in closet, dual sinks, makeup vanity, soaking tub, walk-in shower. Additional main level highlights include a powder room and laundry room. Downstairs offers a spacious family room with fireplace, wet bar, wraparound deck, landscaped lawn, 3 bedrooms, and a full bath. Close to top schools, Hwy 92, CSM, and Laurelwood Shopping Center. Experience the comfort, space, and views this exceptional Tobin Clark residence has to offer. Schedule your showing today!

35 Anguido CT, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: Patrice Carper from Compass

Sold listing courtesy of Stanley Lo from GRBA

$4,200,000
3 Beds 4 Baths ML82006475 MLS
Lower Hillsborough at its best: move-in ready mid-century modern home that was re-imagined in 2017 with an open floor plan,remodeled,kitchen,bathrooms & indoor/outdoor living.At the heart of the home,a custom-made dual-sided fireplace adds a dramatic focal point.The remodeled chef's kitchen equipped with sleek stainless steel appliances(Wolf stove),dual-ovens & custom cabinetry.Floor-to-ceiling dual-paned windows are the highlight of the living room with views of the valley & Bay while formal dining area and piano niche provide warmth with built-in bookshelves.The primary suite with a spa-like bathroom & walk-in closet are on the main level along with one additional bedroom and den, a full bathroom and powder room. Downstairs is your own private oasis with an additional ensuite bedroom,family room,library/game room and access the beautifully landscaped backyard. With a hot tub, fountain, 2 large entertaining patios and views, the outdoor spaces are the perfect complement to the home.The location,with Hillsborough's top ranked public schools,close proximity to San Francisco, Silicon Valley,and easy access to Burlingame shopping/restaurants,makes this an A+ home. County records show 3964 sq ft, Realist 3270 sq ft & floor plan sketch provided by sellers 3390 sq ft.Buyer to satisfy.

525 El Arroyo RD, Hillsborough

Listed by The Patty Dwyer Group, 650-703-1183 from Compass
(If provided) CoList: from

Sold listing courtesy of Victor Lo from SRAI

$5,123,250
5 Beds 4 Baths ML81995860 MLS
If you've been searching for a property with incredible upside, room to grow, and the flexibility to make it truly your own, this is it. Nestled on a large, sunny, and private lot, this 5-bedroom, 4-bathroom French-style estate offers the rare combination of timeless architecture, solid construction, and endless potential. This home is well cared for and move-in ready, but its also a blank canvas for those with imagination. With soaring ceilings, a dramatic southeast-facing entry, and three fireplaces, the home already exudes charm and character thats hard to find. The spacious layout includes a lower level perfect for multigenerational living. The expansive yard has plenty of room for your dream pool, tennis court, garden, or modern outdoor entertaining space. This is a chance to build equity and create something extraordinary in a location that blends peaceful privacy with everyday convenience...just minutes from top-rated schools, shopping, dining, and commuter routes. Bring your ideas and your vision. With the right updates, this could be your forever home and a smart investment!

46 Eugenia WAY, Hillsborough

Listed by Alex Kononoff, 650-207-5341 from eXp Realty of Northern California, Inc.
(If provided) CoList: from

Sold listing courtesy of Annie Liou from NTERO

$8,650,000
7 Beds 9 Baths ML81993380 MLS
Perched atop a serene cul-de-sac in Hillsborough, this architecturally striking modern estate offers breathtaking, unobstructed views of the SF Bay. Built in 2020, this 7 bedroom and 9 baths home blends cutting-edge parametric design with luxurious functionality, creating a seamless flow between indoor and outdoor living. The main residence features 5 beds, 4 full baths, and 2 half baths, thoughtfully designed with high-end finishes and an open-concept layout that maximizes natural light and panoramic vistas. Floor-to-ceiling windows, sleek contemporary lines, and premium materials define the sophisticated ambiance. A separate ADU with its own private entrance adds versatility, offering 2 bedrooms, 2.5 baths, and a stylish, self-contained living space ideal for guests, extended family, or rental income. Nestled in a private and tranquil court, yet just minutes from downtown San Mateo and Burlingame, this home offers the perfect balance of seclusion and convenience. Enjoy an easy commute to major highways, and access to top-rated Hillsborough schools, making this an exceptional opportunity for those seeking both luxury and lifestyle. Approved plans available for a raised infinity edge pool and 500sqft gym. A rare find in one of the Bay Areas most prestigious communities.

30 Melrose Court, Hillsborough

Listed by Vahid Firouzdor, 650-727-4554 from Compass
(If provided) CoList: from

Sold listing courtesy of Jane Konovalova from JETS

$4,750,000
5 Beds 5 Baths ML81959090 MLS
Luxury and Comfort. This Hillsborough gem offers Spectacular Panoramic Bay & Canyon Views from nearly every room! As you enter the house, you will be greeted by a Grand living and dining area featuring a spacious open floor plan, soaring high ceilings, elegant skylights, expansive windows, & glass doors that showcase the breathtaking views that this house offers. The adjacent chefs kitchen is a masterpiece, boasting ample cabinetry, a center island with a built-in sink, a breakfast bar, a second dining area, and a cozy family room w/ a fireplace. After a long day, retreat to one of the several comfortable & relaxing bedrooms. The master suite offers a serene escape w/ picturesque views & a harmonious primary bath with soaking tub. The rear exterior extends the length of the living spaces, providing a versatile and inviting outdoor area for leisure and entertainment. Enjoy a large back deck, patio, and BBQ area, perfect for relaxing and soaking in the breathtaking views from the privacy of your backyard. With its exquisite design, spacious interiors, and a backyard oasis featuring every amenity you could desire, this home offers a lifestyle of comfort and opulence. This house is only less than a 10-minute drive from Downtown Burlingames array of popular shops, restaurants.

1305 Southdown RD, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

$3,698,963
4 Beds 5 Baths ML81967070 MLS
Surrounded by Japanese-inspired landscaping, 35 Lookout Road wows you with expansive sky and hill views from the second you step inside. This authentic Mid-Century Modern invites you into a large open concept living / dining room with sweeping panoramic views through the wall to wall windows, perfect for entertaining. Beautiful kitchen with Island opens to a large breakfast family room, which is truly the heart of this home. Generous Primary Suite with 2 walk-in closets, and 2 bathrooms. Downstairs boasts a total of 3 bedrooms and 2 bathrooms including a large primary with a private entrance and ensuite, downstairs office, loads of storage areas and built-ins throughout. A wet bar / potential kitchenette, large open concept family room and master creates a complete private living suite in of itself. Landscaped grounds are a gardener's dream featuring a beautiful active Koi pond with plenty of room and inspiration for designing your own dream garden.

35 Lookout RD, Hillsborough

Listed by DonnaMarie Baldwin, 650-796-6080 from Compass
(If provided) CoList: from

Sold listing courtesy of DonnaMarie Baldwin from APR

$5,650,600
5 Beds 4 Baths ML81964668 MLS
Every once in a while, a true opportunity presents itself...This Mediterranean masterpiece, feat. rare & spectacular Bridge to Bridge Views, the San Francisco Skyline, Bay Bridge, East Bay Hills, San Francisco Bay, San Mateo Bridge and more at your fingertips! Offering a pristine parcel of land, situated close to downtown, schools, parks, transportation. Here are just some of the attributes to contemplate...Lower Level: Grand Formal entry w/ high ceilings & marble floors, Commanding Living Room w/ Bay Views, full bar & fireplace, Informal Family Room with fireplace, Bay Views and convenient access to the back yard, Spacious Dining room with immediate proximity to the Kitchen, Gourmet Kitchen featuring top quality appliances, natural stone countertops, heated flooring, eat-in area & back yard access, 2 Ground floor suites each w/ spacious bedrooms, hardwood floors & updated bathrooms, Full Laundry facility conveniently located off the Kitchen area. Upper Level: 3 more spacious bedrooms, Expansive Primary Bedroom Suite feat. commanding Bay Views, vaulted ceilings, fireplace, office respite, updated primary bathroom. Outside: Sublime Back yard feat. swimming pool, spa, built-in BBQ/kitchenette, putting green, lawn & entertaining patio, outdoor fireplace & mouth dropping Bay Views!

2500 Summit DR, Hillsborough

Listed by Gregory Terry, 650-678-1110 from Compass
(If provided) CoList: from

Sold listing courtesy of Bradley Joe from COMP

$6,750,000
5 Beds 6 Baths ML81945604 MLS
BEST DEAL DONT MISS OUT!!!!! ONE OF THE BEST VIEWS IN ALL OF HILLSBOROUGH! UNPARALLELED PANORAMIC BAY VIEWS from nearly every part of the house. 270 DEGREE+ UNOBSTRUCTED VIEWS! Experience breathtaking sunrises & sunsets right from the backyard. Embrace the good life w/ this one-of-a-kind showcase home. Contemporary design culminates w/ modern conveniences in a fantastic open floor plan; this is the pinnacle of luxury living! The home itself sits on an expansive 1.3 acre lot at the end of a private cul-de-sac. The sophisticated foyer sets the tone for the entire residence. Inside you'll find high ceilings, crown molding, recessed lightings, skylights, hardwood flooring, a semi-spiral staircase, central ac, a movie room, office, wine cellar, family room, wet bar, multiple en-suite bedrooms, high-end appliances, big living room, and more. The chef's kitchen is a masterpiece of design & functionality. There's a separate au-pair / in-law unit w/ its own access. There's a huge flat backyard overlooking everything!

30 Miranda CT, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

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